1024+ Private Villas and Holiday Rentals in Oak Square |
  1. USA
  2. Massachusetts
  3. Boston
  4. Oak Square

Oak Square Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Oak Square

Discover more than 1024 vacation rentals available in Oak Square. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oak Square.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oak Square, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oak Square. On average, places to stay near Oak Square offer 603.08 ft², with nightly prices averaging ZA R5,559.

With Casai, finding and comparing holiday rentals in Oak Square is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Oak Square

Type Count
Holiday Apartments 661
Vacation Homes 193
Cottages 1
Villas 1

Use these Quick Filters to Find a Holiday Rental in Oak Square

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Oak Square.

Weather in Oak Square, MA

View the weather forecast for Oak Square before booking your Oak Square Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Frequently Asked Questions About Oak Square?

What are the top holiday rentals in Oak Square?

With numerous options available in Oak Square, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oak Square:

How many holiday rentals have private pools in Oak Square?

Discover a selection of holiday rentals with private pools near Oak Square with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Oak Square are best for families?

If you're searching for a family-friendly holiday home in Oak Square, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Oak Square:

How many Casai.co.za holiday rentals are available in Oak Square?

As of 2026, Casai boasts over 1024 properties listed in the Oak Square area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oak Square.

Nearby Neighborhood (7) 
Neighborhood Property Count
Brighton Vacation Rentals in Boston, Massachusetts 92
Cleveland Circle Vacation Rentals in Boston, Massachusetts 75
Allston Vacation Rentals in Boston, Massachusetts 55
St. Elizabeth's Vacation Rentals in Boston, Massachusetts 47
Commonwealth Vacation Rentals in Boston, Massachusetts 30
Newton Corner Vacation Rentals in Boston, Massachusetts 499
Hunnewell Hill Vacation Rentals in Boston, Massachusetts 622

People Also Ask

There are 1024 Oak Square, MA Holiday Rentals

Recently Booked Holiday Rentals in Oak Square